Mono-azodyestuffs



iaiented Jan. 19, 1937 UNITED STATES PATENT @E'MCE 2,068,172 MONO-AZODYESTUFFS Richard Fleischhauer, Frankfort-on-the-Main- Fechenheim,

Germany, assignor to General Aniline Works, Inc., New York, N. Y., a corporation of Delaware No Drawing.

Serial No. 757,070. 1933 2 Claims.

This invention relates to mono-azodyestuffs, more particularly to those corresponding to the general formula:

OH NH-C O-R Y I /acyl and -N aralky acyl acyl cyclohexyl phenyl Y is selected from the group consisting of hydrogen, methyl, chlorine and a sulfonic acid group and R is selected from thegroup consisting of methyl, methoxymethyl, phenoxymethyl and phenyl.

These dyestufis are obtained by combining a diazo-compound of an aromatic amine corresponding to the formula:

wherein X has the above signification and the nucleus may contain substituents of the aforesaid type, with an l-acyl-amino-S-hydroxynaphthalene-G-sulfonic acid.

In comparison to known analogous dyestuffs the dyestuffs of the present invention are distinguished partly by a better leveling power, partly by a better fastness to light.

The present invention represents a valuable enrichment of the industry. According to the invention bluish red dyestuffs are obtained of a very good leveling power and fastness to light which are especially suitable for dyeing animal fibers but may also be used for other dyeing purposes.

The components used may be varied in such a manner that e. g. the acyl-amino-group con- Application December 11, 1934, In Germany December 23,

tains the following residues: methyl, ethyl, propyl,

butyl, benzyl, cyclohexyl and soon, further phenyl and its substitution products. As acyl residues for example acetyl, methoxyacetyl, phenoxyacetyl, benzoyl, benzene-sulfonyl and their substitution products or also the urethane group may be named.

In order to further illustrate my invention the following examples are given, the parts being by weight and all temperatures in centigrade degrees; but I wish it, however, to be understood that my invention is not limited to the examples given, nor to the exact conditions stated therein.

Example 26.8 parts of N-butyl-benzoylaminol-aminobenzene are diazotized and the almost colorless diazo solution thus obtained is allowed to run in while stirring at about 10 C. into a solution of 29 parts of 1-acetylamino-8-naphthol-6-sulfonic acid to which an excess of sodium acetate has been added. The dyestuff thus obtained is when dry a brownish red water soluble powder and dyes wool very level bright bluish red shades of a good fastness. It corresponds to the formula:

(IJH ITIHCOCH:

I claim: 1. Monoazodyestuffs of the general formula,

HOSS

10 wherein X is selected from the group consisting acyl acyl I N y alkyl cyclohexyl sisting of methyl, methoxymethyl, phenoxymethyl and phenyl, which dyestufis are when dry reddish water soluble powders and dye the animal fibers bluish red shades of a. very good leveling power and fastness to light.

2. The monoazodyestufi of the formula,

0 H N HC 0 O H: O I

HOaS

which is when dry a brownish red water soluble powder and dyes wool very level bright bluish red shades of a good fastness.

RICHARD FLEISCHHAUER. 

